Binaphthyl-arylamine polymers
View Patent ↗Disclosed are Binaphthyl-Arylamine Polymers having Formula I: In the Formula: Ar 1 is an arylene; Ar 2 is an aryl group; Ar 3 is an arylene; Binap is a binaphthyl moiety; M is a conjugated moiety; and x, y and z are mole fractions such that x+y+z=1.0, with the proviso that x and y are not zero.
1. A copolymer having Formula I:
wherein:
M is the same or different at each occurrence and is selected from the group consisting of an aromatic unit having triarylamine units and an aromatic unit having a crosslinkable substituent; and
x, y and z are mole fractions such that x+y+z=1.0, with the proviso that x and y are not zero;
wherein Binap is a 1,1′-binaphthyl group having a formula selected from the group consisting of Formula IIa, Formula IIc, Formula IId, and Formula IIe
where:
* represents a point of attachment to the other units in the compound;
R 1 is the same or different at each occurrence and is selected from the group consisting of H, D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups, or the two R 1 groups may be joined together to form an aliphatic ring having 5-10 carbons;
R 2 is the same or different at each occurrence and is selected from the group consisting of D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups; and
a is the same or different at each occurrence and is an integer from 0-5;
wherein Ar 1 is selected from the group consisting of phenylene, p-biphenylene, p-terphenylene, naphthylene, phenylenenaphthylene, naphthylenephenylene and a group having Formula III
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4; and
m is the same or different at each occurrence and is an integer from 1 to 6;
wherein Ar 2 is selected from the group consisting of naphthyl and a group having Formula IV
where:
d is the same or different at each occurrence and is an integer from 0-5;
and wherein Ar 3 is selected from the group consisting of naphthylene and a group having Formula III.
2. The copolymer of claim 1 , wherein R 1 is selected from an alkyl group having 1-12 carbon atoms and an alkoxy group having 1-12 carbon atoms.
3. The copolymer of claim 1 , wherein R 2 is selected from an alkyl group having 1-12 carbon atoms and an alkoxy group having 1-12 carbon atoms.
4. The copolymer of claim 1 , wherein crosslinking substituents are present on at least one Ar 2 .
5. The copolymer of claim 1 , wherein x and y are each in the range of 0.4 to 0.6.
6. The copolymer of claim 1 , wherein z is not zero.
7. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer and an active layer therebetween, wherein the active layer comprises a copolymer having Formula I:
wherein:
M is the same or different at each occurrence and is selected from the group consisting of an aromatic unit having triarylamine units and an aromatic unit having a crosslinkable substituent; and
x, y and z are mole fractions such that x+y+z=1.0, with the proviso that x and y are not zero;
wherein Binap is a 1,1′-binaphthyl group having a formula selected from the group consisting of Formula IIa, Formula IIc, Formula IId, and Formula IIe
where:
* represents a point of attachment to the other units in the compound;
R 1 is the same or different at each occurrence and is selected from the group consisting of H, D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups, or the two R 1 groups may be ioined together to form an aliphatic ring having 5-10 carbons;
R 2 is the same or different at each occurrence and is selected from the group consisting of D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups; and
a is the same or different at each occurrence and is an integer from 0-5;
wherein Ar 1 is selected from the group consisting of phenylene, p-biphenylene, p-terphenylene, naphthylene, phenylenenaphthylene, naphthylenephenylene and a group having Formula III
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4; and
m is the same or different at each occurrence and is an integer from 1 to 6;
wherein Ar 2 is selected from the group consisting of naphthyl and a group having Formula IV
where:
d is the same or different at each occurrence and is an integer from 0-5;
and wherein Ar 3 is selected from the group consisting of naphthylene and a group having Formula III.
8. The device of claim 7 , wherein R 1 is selected from an alkyl group having 1-12 carbon atoms and an alkoxy group having 1-12 carbon atoms.
9. The device of claim 7 , wherein R 2 is selected an alkyl group having 1-12 carbon atoms and an alkoxy group having 1-12 carbon atoms.
10. The device of claim 7 , wherein a crosslinking substituent is present on at least one Ar 2 .
11. The device of claim 7 , wherein x and y are each in the range of 0.4 to 0.6.
12. The device of claim 7 , wherein z is not zero.
13. The device of claim 7 , wherein the active layer is a hole transport layer and the layer consists essentially of a copolymer having Formula I.
14. The device of claim 7 , wherein the active layer is a photoactive layer.
15. The device of claim 14 , wherein the active layer further comprises a photoactive material.
16. The device of claim 15 , wherein the photoactive layer consists essentially of the photoactive material and a copolymer having Formula I.
17. A copolymer which is Compound A
Compound A